Granted Patent B1

US 12,521,703 · App. 18/995,171 · Granted Jan 13, 2026

Inventors: Benjamin David Herzog (Wichita, KS); William J. Tenn, III (Beaumont, TX)

Assignee: INV Nylon Chemicals Americas, LLC

B01J31/2295B01J2231/322B01J2231/52B01J2531/50

Abstract

Claims (36)

1 . A process for the hydrocyanation of an organic compound containing at least one olefinic group comprising reacting the organic compound with hydrogen cyanide in the presence of a catalyst complex comprising at least one transition metal and a ligand containing arsenic and having the formula (I):

wherein

n is 1 and the ligand is monodentate or n is 2 and the ligand is bidentate,

each X is O or NH, and

Ar 1 and Ar 2 is the same or different and each is an aryl group, and each Ar 1 group connected to the same As atom are separate aryl groups or are combined to form a single aryl group.

2 . The process of claim 1 , wherein the organic compound comprises 1,3-butadiene.

3 . The process of claim 1 , wherein the organic compound comprises 3-pentenenitrile.

4 . The process of claim 1 , wherein a product of the hydrocyanation of the organic compound is a monoethylenically unsaturated compound, wherein the process further comprises double bond isomerization of the monoethylenically unsaturated compound comprising contacting the monoethylenically unsaturated compound with the catalyst complex.

5 . The process of claim 4 , wherein the monoethylenically unsaturated organic compound comprises 2-methyl-3-butenenitrile.

6 . The process of claim 1 , wherein n is 2 and the ligand is bidentate.

7 . The process of claim 1 , wherein each X is O.

8 . The process of claim 1 , wherein each X is NH.

9 . The process of claim 1 , wherein each Ar 1 comprises a phenyl group substituted with one or more alkyl groups having from 1 to 4 carbon atoms.

10 . The process of claim 1 , wherein each Ar 1 is xylyl or 2-isopropyl-5-methylphenyl.

11 . The process of claim 1 , wherein each Ar 2 group is optionally substituted phenyl or naphthyl, wherein the phenyl rings or naphthyl rings are bonded to one another to form a biphenyl group or binaphthyl group.

12 . The process of claim 1 , wherein the ligand has a structure according to formula (I) or formula (II):

wherein

X is O or NH,

each R 1 is independently selected from H and alkyl groups having from 1 to 4 carbon atoms, or all but one R 1 group on each phenyl ring is independently selected from H and alkyl groups having from 1 to 4 carbon atoms and the remaining R 1 group is missing and replaced by a single bond linking two of the phenyl rings, and

each R 2 is independently selected from H, alkyl groups having 1-6 carbon atoms and alkoxy groups having 1-6 carbon atoms.

13 . The process of claim 12 , wherein all X groups are O or all X groups are NH.

14 . The process of claim 12 , wherein each R 1 is independently selected from H, methyl and isopropyl, or all but one R 1 group on each phenyl ring is independently selected from H, methyl and isopropyl, and the remaining R 1 group is missing and replaced by a single bond linking two of the phenyl rings; and each R 2 is independently selected from H, alkyl groups having 1-4 carbon atoms and alkoxy groups having 1-4 carbon atoms.

15 . The process of claim 1 , wherein the ligand contains arsenic and has one of the following structures:

16 . The process of claim 1 , wherein the at least one transition metal comprises nickel.

17 . A process for double bond isomerization of a monoethylenically unsaturated compound comprising contacting said compound with a catalyst complex comprising at least one transition metal and a ligand containing arsenic and having the formula (I):

wherein

n is 1 and the ligand is monodentate or n is 2 and the ligand is bidentate,

each X is O or NH, and

Ar 1 and Ar 2 are the same or different and each is an aryl group, and each Ar 1 group connected to the same As atom are separate aryl groups or are combined to form a single aryl group.

18 . A ligand containing arsenic and having the formula (I):

wherein

n is 2 and the ligand is bidentate,

each X is O or NH, and

Ar 1 and Ar 2 are the same or different and each is an aryl group, and each Ar 1 group connected to the same As atom are separate aryl groups or are combined to form a single aryl group.

19 . The ligand of claim 18 containing arsenic and having one of the following structures:

20 . A catalyst complex comprising the ligand as claimed in claim 18 and at least one transition metal comprising nickel.

Assignments (1)

Priority Claims (1)

Continuity (1)

References Cited (95)